57664-71-8

Upstream product

• 18733-07-8 (2-hydroxyphenyl)(4-methoxyphenyl)methanone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 533-58-4 2-Iodophenol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 923595-16-8 3-(4-methoxyphenyl)-2,3-dihydrobenzofuran-3-ol 
• 88275-87-0 3-bromo-2-methyloxybenzaldehyde 
• 1829-34-1 2-hydroxy-3-bromobenzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 59214-70-9 3-bromobenzofuran 
• 5720-07-0 4-methoxyphenylboronic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 108-95-2 phenol 
• 696-62-8 para-iodoanisole 
• 90-02-8 salicylaldehyde 

Relevant academic research and scientific papers

Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives

A nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.

Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles

The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.

Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis

Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5)and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29)as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.

Exogenous-oxidant-free electrochemical oxidative C-H sulfonylation of arenes/heteroarenes with hydrogen evolution

An efficient and environmentally benign electrochemical oxidative radical C-H sulfonylation of arenes/heteroarenes was developed in this work. A series of significant diarylsulfones were prepared under mild catalyst- and exogenous-oxidant-free reaction conditions, which efficiently avoid the issues of desulfonylation or over-reduction of sulfonyl groups.

Mechanistic Insights on Orthogonal Selectivity in Heterocycle Synthesis

Recently, we have developed a method for catalytic regioselective synthesis of 2-substituted and 3-substituted benzofurans starting from phenols. The choice of reacting partner, olefin versus α,β-unsaturated acid, is critical to dictate the isomeric product formation. Instances are known where these olefinic partners did not complement each other and yield a similar outcome. In the current work, we have addressed this paradox with emphasis on (a) the origin of orthogonal selectivity and (b) the key requirements to expect complementary behavior. Experimental and computational studies provided important mechanistic insights. Electrostatic compatibility during migratory insertion and the positioning of the carboxylic acid moiety in catalytic steps are found to exert a paramount impact in determining the regioselectivity. The study offers a predictable single component tuning tool to control the regioselectivity.

Orthogonal selectivity with cinnamic acids in 3-substituted benzofuran synthesis through C-H olefination of phenols

A palladium catalyzed intermolecular annulation of cinnamic acids and phenols has been achieved for the selective synthesis of 3-substituted benzofurans. Isotope labeling, competition experiments, kinetic studies, and intermediate trapping have supported a sequence of C-C bond formation and decarboxylation followed by the C-O cyclization pathway. This journal is

Benzofurans from benzophenones and dimethylacetamide: Copper-promoted cascade formation of furan O1-C2 and C2-C3 bonds under oxidative conditions

DMA donates: Copper(II) acetate and 8-hydroxyquinoline promote the formation of a benzofuran core through a cascade of copper-catalyzed processes wherein the key carbon atom comes from the dimethylacetamide (DMA) solvent. Strong evidence for the participation of a Wacker cyclization catalyzed solely by copper is provided, not only in the title reaction from benzophenones but also from 2-hydroxy-α-arylstyrene derivatives. Copyright

Palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones

A palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones was developed. Compared to Pd(OAc)2 catalysis system, cationic palladium complex with dppp as the ligand has higher catalytic activity and efficiency for wider sc

Reactions of 2-hydroxybenzophenones with Corey-Chaykovsky reagent

A variety of 2-hydroxybenzophenones on reaction with Corey-Chaykovsky reagent underwent unprecedented rearrangements leading to 3-substituted benzofurans 8 and one-carbon homologated compounds 9 and 12. Compounds 9 could further be quantitatively transfor

Halogen-metal exchange/cyclization of iodoketones: A direct synthesis of 3-arylbenzofurans

The first synthesis of benzofuran 2 was achieved in 17% overall yield in seven steps. The key step was a halogen-metal exchange/cyclization reaction. Several examples of this reaction were reported. Georg Thieme Verlag Stuttgart.